CA1215371A - Composes heterocycliques d'aralcoylaminoethanol - Google Patents

Composes heterocycliques d'aralcoylaminoethanol

Info

Publication number: CA1215371A
Authority: CA; Canada
Prior art keywords: amino; methyl; phenylpropyl; pyridinemethanol; alpha
Prior art date: 1982-10-01
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000412664A

Other languages

English (en)

Inventor

Joseph G. Atkinson

David E. Mcclure

John J. Baldwin

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Merck Sharp and Dohme IA Corp

Merck and Co Inc

Original Assignee

Merck Sharp and Dohme IA Corp

Merck and Co Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1982-10-01

Filing date

1982-10-01

Publication date

1986-12-16

1982-10-01 Application filed by Merck Sharp and Dohme IA Corp, Merck and Co Inc filed Critical Merck Sharp and Dohme IA Corp

1982-10-01 Priority to CA000412664A priority Critical patent/CA1215371A/fr

1986-12-16 Application granted granted Critical

1986-12-16 Publication of CA1215371A publication Critical patent/CA1215371A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 50
-1 Heterocyclic aminoethanols Chemical class 0.000 claims abstract description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
238000000034 method Methods 0.000 claims description 22
238000002360 preparation method Methods 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
239000000126 substance Substances 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 claims description 3
230000003301 hydrolyzing effect Effects 0.000 claims 7
229910021626 Tin(II) chloride Inorganic materials 0.000 claims 3
235000011150 stannous chloride Nutrition 0.000 claims 3
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims 2
QJJHHYOORRITQD-UHFFFAOYSA-N 5-[1-hydroxy-2-[(2-methyl-4-phenylbutan-2-yl)amino]ethyl]-1h-pyridin-2-one Chemical compound C1=CC(=O)NC=C1C(O)CNC(C)(C)CCC1=CC=CC=C1 QJJHHYOORRITQD-UHFFFAOYSA-N 0.000 claims 2
239000001119 stannous chloride Substances 0.000 claims 2
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims 1
239000003814 drug Substances 0.000 abstract description 10
150000002391 heterocyclic compounds Chemical class 0.000 abstract description 4
125000000623 heterocyclic group Chemical group 0.000 abstract description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
229910001868 water Inorganic materials 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
239000000203 mixture Substances 0.000 description 22
229940093499 ethyl acetate Drugs 0.000 description 20
235000019439 ethyl acetate Nutrition 0.000 description 20
239000012458 free base Substances 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 15
229920000642 polymer Polymers 0.000 description 15
235000002639 sodium chloride Nutrition 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 12
239000000047 product Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
239000007787 solid Substances 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
229910017974 NH40H Inorganic materials 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
238000010992 reflux Methods 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
230000000903 blocking effect Effects 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
230000004410 intraocular pressure Effects 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
238000003756 stirring Methods 0.000 description 6
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
239000004014 plasticizer Substances 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
239000003981 vehicle Substances 0.000 description 5
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
208000010412 Glaucoma Diseases 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
206010020772 Hypertension Diseases 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000002253 acid Substances 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
150000002688 maleic acid derivatives Chemical class 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
239000004372 Polyvinyl alcohol Substances 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229920002125 Sokalan® Polymers 0.000 description 3
239000000674 adrenergic antagonist Substances 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
230000007883 bronchodilation Effects 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000026030 halogenation Effects 0.000 description 3
238000005658 halogenation reaction Methods 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 3
239000001863 hydroxypropyl cellulose Substances 0.000 description 3
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 3
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 3
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 3
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 3
239000011976 maleic acid Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
229920000609 methyl cellulose Polymers 0.000 description 3
235000010981 methylcellulose Nutrition 0.000 description 3
239000001923 methylcellulose Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
150000002924 oxiranes Chemical class 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
229920002451 polyvinyl alcohol Polymers 0.000 description 3
235000019422 polyvinyl alcohol Nutrition 0.000 description 3
229940068984 polyvinyl alcohol Drugs 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
229920003169 water-soluble polymer Polymers 0.000 description 3
PRJWYFPDHWJLEV-UHFFFAOYSA-N 2-methyl-4-phenylbutan-2-amine Chemical compound CC(C)(N)CCC1=CC=CC=C1 PRJWYFPDHWJLEV-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
ACFYAUKMPJWHID-UHFFFAOYSA-N 7-acetyl-4h-1,4-benzoxazin-3-one Chemical compound N1C(=O)COC2=CC(C(=O)C)=CC=C21 ACFYAUKMPJWHID-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
125000006519 CCH3 Chemical group 0.000 description 2
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
229910021590 Copper(II) bromide Inorganic materials 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
241000282414 Homo sapiens Species 0.000 description 2
239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
239000007832 Na2SO4 Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
230000003276 anti-hypertensive effect Effects 0.000 description 2
206010003119 arrhythmia Diseases 0.000 description 2
230000006793 arrhythmia Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
229910021538 borax Inorganic materials 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229940124630 bronchodilator Drugs 0.000 description 2
239000006172 buffering agent Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000000969 carrier Substances 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
229960001701 chloroform Drugs 0.000 description 2
238000013329 compounding Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
235000012489 doughnuts Nutrition 0.000 description 2
230000002526 effect on cardiovascular system Effects 0.000 description 2
238000010828 elution Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000010408 film Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
235000010339 sodium tetraborate Nutrition 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
230000004936 stimulating effect Effects 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000000829 suppository Substances 0.000 description 2
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 2
229940033663 thimerosal Drugs 0.000 description 2
239000010409 thin film Substances 0.000 description 2
FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 2
238000001665 trituration Methods 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
WECUIGDEWBNQJJ-SECBINFHSA-N (2r)-4-phenylbutan-2-amine Chemical compound C[C@@H](N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-SECBINFHSA-N 0.000 description 1
DYIOSHGVFJTOAR-JGWLITMVSA-N (2r,3r,4s,5r)-6-sulfanylhexane-1,2,3,4,5-pentol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CS DYIOSHGVFJTOAR-JGWLITMVSA-N 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
HAFWELDDNUXLCK-TYYBGVCCSA-N (e)-but-2-enedioic acid;hydrate Chemical compound O.OC(=O)\C=C\C(O)=O HAFWELDDNUXLCK-TYYBGVCCSA-N 0.000 description 1
VVOYCNVZJXQFBB-BTJKTKAUSA-N (z)-but-2-enedioic acid;6-[1-hydroxy-2-(4-phenylbutan-2-ylamino)ethyl]-4h-1,4-benzoxazin-3-one Chemical compound OC(=O)\C=C/C(O)=O.C=1C=C2OCC(=O)NC2=CC=1C(O)CNC(C)CCC1=CC=CC=C1 VVOYCNVZJXQFBB-BTJKTKAUSA-N 0.000 description 1
NSLXKPWIPPFALT-BTJKTKAUSA-N (z)-but-2-enedioic acid;7-[1-hydroxy-2-(4-phenylbutan-2-ylamino)ethyl]-4h-1,4-benzoxazin-3-one Chemical compound OC(=O)\C=C/C(O)=O.C=1C=C2NC(=O)COC2=CC=1C(O)CNC(C)CCC1=CC=CC=C1 NSLXKPWIPPFALT-BTJKTKAUSA-N 0.000 description 1
JCIIKRHCWVHVFF-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine;hydrochloride Chemical compound Cl.NC1=NC=NS1 JCIIKRHCWVHVFF-UHFFFAOYSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
UXSNZYGTQTXRAD-UHFFFAOYSA-N 1-(6-chloropyridin-3-yl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)N=C1 UXSNZYGTQTXRAD-UHFFFAOYSA-N 0.000 description 1
DDBLPTNLEVQANE-UHFFFAOYSA-N 1-(tetrazolo[1,5-a]pyridin-6-yl)ethanone Chemical compound C1=C(C(=O)C)C=CC2=NN=NN21 DDBLPTNLEVQANE-UHFFFAOYSA-N 0.000 description 1
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AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
229940001474 sodium thiosulfate Drugs 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
229940035044 sorbitan monolaurate Drugs 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229960004418 trolamine Drugs 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000412664A 1982-10-01 1982-10-01 Composes heterocycliques d'aralcoylaminoethanol Expired CA1215371A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000412664A CA1215371A (fr)	1982-10-01	1982-10-01	Composes heterocycliques d'aralcoylaminoethanol

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000412664A CA1215371A (fr)	1982-10-01	1982-10-01	Composes heterocycliques d'aralcoylaminoethanol

Publications (1)

Publication Number	Publication Date
CA1215371A true CA1215371A (fr)	1986-12-16

Family

ID=4123703

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000412664A Expired CA1215371A (fr)	1982-10-01	1982-10-01	Composes heterocycliques d'aralcoylaminoethanol

Country Status (1)

Country	Link
CA (1)	CA1215371A (fr)

1982
- 1982-10-01 CA CA000412664A patent/CA1215371A/fr not_active Expired

Publication	Publication Date	Title
US4358455A (en)	1982-11-09	Aralkylamindethanol heterocyclic compounds
US5112820A (en)	1992-05-12	Anti-glaucoma compositions containing 2- and 3-aminomethyl-6-arylcarbonyl- or 6-phenylthio-2,3-dihydropyrrolo-(1,2,3-de)-1,4-benzoxazines and method of use thereof
US4430343A (en)	1984-02-07	Benzimidazole derivatives, process for the preparation thereof and pharmaceutical composition containing the same
US4501890A (en)	1985-02-26	Trans-(±)-2,4,6-substituted-5,5a,6,7,8,9,9a,10-octahydro-pyrimido[4,5-g]quinolines
JPS63122675A (ja)	1988-05-26	抗潰瘍剤として活性な新規ベンズイミダゾール誘導体
US4730042A (en)	1988-03-08	Compounds 1 or 3-hydroxy-4-benzyl-6-methyl-7-(4-isopropylamino-butoxy)-1,3-dihydro[3,4-C]pyridine and 2-methyl-3-(4-isopropyl-aminobutoxy)-4-(1'-morphilinomethyl)-5-hydroxymethyl-6-benzyl pyridine, useful for treating cardiac arrhythmias
KR870001072B1 (ko)	1987-05-27	옥타하이드로티아졸로[4,5-g] 퀴놀린의 제조방법
EP0105053B1 (fr)	1988-01-20	Composés hétérocycliques d'aralkylaminoéthanol
GB2041925A (en)	1980-09-17	2-substituted-trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido (4,3-b)indoles
US4568679A (en)	1986-02-04	Aralkylaminoethanol heterocyclic compounds
US4816457A (en)	1989-03-28	Aralkylaminoethanol heterocyclic compounds
CA1084918A (fr)	1980-09-02	Obtention de 5,11-dihydro-6h-pyrido 2,3,b - 1,4 benzoidazepin-6-ones substituees en 11; produits pharmaceutiques qui les contiennent
US4442094A (en)	1984-04-10	(3-Aralkylamino-2-or-propoxy)heterocyclic compounds
US4656168A (en)	1987-04-07	(3-aralkylamino-2-or-propoxy)heterocyclic compounds in method of effecting bronchodilation
US4686222A (en)	1987-08-11	Aralkylaminoethanol heterocyclic compounds
US4348398A (en)	1982-09-07	Quinolinyl ethanolamines
JPH10139780A (ja)	1998-05-26	新規な複素環式アミノメチル化合物、これらの製造方法及びこれらを含む医薬組成物
CA1215371A (fr)	1986-12-16	Composes heterocycliques d'aralcoylaminoethanol
JPS63192778A (ja)	1988-08-10	β−アドレナリン受容体遮断薬としてのピペラジニルピリミジン類
CA1208643A (fr)	1986-07-29	Composes a base de 1,5-diphenyl-pyrazolin-3-one; methode et produits intermediaires pour la preparation; compositions pharmaceutiques qui renferment ces composes
US3978064A (en)	1976-08-31	3-Aminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid esters and intermediates leading thereto
US4472427A (en)	1984-09-18	(Aralkylamino-2-OR-propoxy)heterocyclic compounds
CA1207774A (fr)	1986-07-15	Composes a base de 1-phenylindazol-3-one; methode de preparation et preparations pharmaceutiques qui renferment ces composes
US4349673A (en)	1982-09-14	Benzoxazines
JPH03120271A (ja)	1991-05-22	抗虚血活性を有するフェニルアルキルアミン誘導体

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